It is known to modify the bulk and surface properties of polymers with the use of monomers having side groups and/or functional groups. For instance, the use of fluorinated vinyl ethers as monomers in the preparation of fluorinated polymers has been extensively described; e.g. CARLSON, Peter, et al. Organic Fluoropolymers; Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH Verlag, 2000. p. 495-533.
The bulkiness of the —OSF5 moiety in the side chain of monomeric units may provide advantages in the modification of the crystallinity and of the surface properties of fluorinated polymers or of fluorinated compounds in general. Compounds comprising the —OSF5 moiety might also find use in the preparation of surface active agents, such as surfactants.
So far, however, the preparation of only one fluorinated unsaturated compound comprising the —OSF5 moiety, namely CF2═CFCF2OSF5, has been achieved, see WO 2013/000735 A (SOLVAY SPECIALTY POLYMERS ITALY SPA) 3 Jan. 2013.
The synthesis of other fluorinated unsaturated compounds comprising the —OSF5 moiety via the direct addition of SOF4 to a fluorinated unsaturated compound has so far been unsuccessful in standard conditions, see DU, L., et al. Synthesis of pentafluorosulfanyl trifluorovinyl ether and its facile rearrangement to difluoro(pentafluorosulfanyl)acetyl fluoride. Angew. Chem., Int. Ed. Engl. 2007, vol. 46, p. 6626-6628.
MARCELLIS, Alphonso W., et al. Synthesis of pentafluorosulfuroxydifluoroacetly fluoride. Journal of Fluorine Chemistry. 1975, vol. 5, p. 71-75. teaches to prepare SF5OCF2C(O)F by the action of both ozone and oxygen on the olefin SF5CF═CF2.
SCHACK, Carl J., et al. Introduction of functional Groups into Some Chlorofluorocarbon Ethers. Journal of Fluorine Chemistry. 1979, vol. 14, p. 519-522. discloses SF5OCF2C(O)F, which is prepared by addition of SF5OCl to a perfluoroolefin.
EP 1889832 A (AIR PROD & CHEM) 20 Feb. 2008 discloses compositions that may comprise a molecular compound of the formula ZOSF5, wherein Z is a member selected from C1-20 alkyl, aryl, cycloalkyl, combinations thereof, and analogues containing at least one halogen and/or heteroatom (page 2, par. [0004]). The compound ZOSF5 can be obtained by addition of the OSF5 function to a compound ZL, wherein L is a leaving group and Z is as defined above, by way of a nucleophilic displacement reaction (page 2, par. [0009] and page 3, par. [0013]).
DE 102011114650 (MERCK PATENT GMBH) 3 May 2012 relates to compounds comprising —OSF5 end groups, including certain compounds complying with formula (III) reported on page 14. The compounds of formula (III) are prepared by addition of SF5OCl to an olefin or by nucleophile substitution of triflates with, for instance, TAS+F5SO−.
CASE, J. R., et al. Pentafluorosulpuroxy-derivatives of Hexafluoropropene. Journal of the Chemical Society. 1964, no. 946, p. 948. discloses the reaction of bispentafluorosulphur peroxide and pentafluorosulphur hypofluorite with hexafluoropropene to give a series of compounds SF5O[C3F6]nOSF5 where n=2, 3, or 4.
A new method for the preparation of fluorinated compounds comprising the pentafluorosulfanyl moiety —OSF5, as starting materials for the preparation of a wide range of novel fluorinated compounds comprising —OSF5 groups, has now been found.